有机化学oRcAn1©©ⅫEMISTRY 主：王德儒870928290) 理学院寇化素理科接2层26 Organic Chemistry,6th Edition L.G.Wade,Jr. Chapter 14 I15 Alcohols Key Notes Hydrogen bonding;Acidity;Lucas reagent; Dehydration;Williamson synthesis Homework: 14-29;14-30:e,g,h,Ij,l,m:14-32:b,c:14-37:b(P495) 15-27:c;15-28;15-37:a,c,e(P529):
Chapter 14 & 15 Alcohols Organic Chemistry, 6th Edition L. G. Wade, Jr. Key Notes Hydrogen bonding; Acidity; Lucas reagent ; Dehydration ; Williamson synthesis 有机化学ORGANIC CHEMISTRY 主讲：王俊儒 87092829(O) 理学院应化系理科楼2层C206 Homework: 14-29；14-30: e,g,h,I,j,l,m；14-32: b,c；14-37: b(P495)； 15-27: c；15-28；15-37: a,c,e (P529);
CONTENTS Structure Properties of Alcohols Preparation of alcohols Functional group transformation ■C-C bond formation Reduction of Carbonyl Rxns of Alcohols ■Acid-base reactions Elimination:Dehydration to alkene ■ Synthesis of alkyl halides:Substitution to form alkyl halide Oxidation to aldehyde,ketone ■Reduction to alkane -Synthesis of mesylate and tosylates ■Esterification Williamson synthesis of ether
CONTENTS ❖Structure & Properties of Alcohols ❖Preparation of alcohols ◼ Functional group transformation ◼ C-C bond formation ◼ Reduction of Carbonyl ❖Rxns of Alcohols ◼ Acid-base reactions ◼ Elimination:Dehydration to alkene ◼ Synthesis of alkyl halides: Substitution to form alkyl halide ◼ Oxidation to aldehyde, ketone ◼ Reduction to alkane ◼ Synthesis of mesylate and tosylates ◼ Esterification ◼ Williamson synthesis of ether
Sec 1 Structure Properties of Alcohols 0.96A 1.4 0.96A H 104.5° H 108.9° water water water H H methyl alcohol methyl alcohol methyl alcohol Copyright2010 Pearson Prentice Hall,Inc. Hydroxyl(-OH)functional group Oxygen is sp3 hybridized. The H-O-H angle in water is 104.5. The C-O-H angle in methyl alcohol is 108.9. 1、-C,O;SP3 hybridized;O:不等性SP杂化 2、-O-H,C-O为极性共价键 3、-OH,-R-,+I
Sec 1 Structure & Properties of Alcohols ❖Hydroxyl (-OH) functional group ❖Oxygen is sp3 hybridized. ❖The H—O—H angle in water is 104.5°. ❖The C—O—H angle in methyl alcohol is 108.9°. 1、－C，O； SP3 hybridized; O:不等性SP3杂化 2、－O-H，C-O为极性共价键 3、－OH, -I; R-, +I
Physical Properties H Alcohols are polar compounds.They interact with themselves and with other polar compounds by dipole- dipole interactions. Dipole-dipole interaction:the attraction between the positive end of one dipole and the negative end of another. -Unusually high boiling points due to hydrogen bonding between molecules. -Small alcohols are miscible in water,but solubility decreases as the size of the alkyl group increases. 00 H H 0 1u=1.69D 0=1.30D u=0.08D H CH,CH, HC CH H.C CH ethanol,MW 46 dimethyl ether,MW 46 propane,MW 44 bp78℃ bp-25C bp-42C
Physical Properties - + + O H H H C H ❖Alcohols are polar compounds. They interact with themselves and with other polar compounds by dipoledipole interactions. ❖Dipole-dipole interaction: the attraction between the positive end of one dipole and the negative end of another. ◼Unusually high boiling points due to hydrogen bonding between molecules. ◼Small alcohols are miscible in water, but solubility decreases as the size of the alkyl group increases
Physical Properties Hydrogen bonding:when the positive end of one dipole is an H bonded to F,O,or N (atoms of high electronegativity)and the other end is F,O, or N -the strength of hydrogen bonding in water is approximately 21 kJ (5 kcal)/mol hydrogen bonds are considerably weaker than covalent bonds -nonetheless,they can have a significant effect on physical properties Alcohol ether ydrogen bond R hydrogen bond donor acceptor
Physical Properties ❖Hydrogen bonding: when the positive end of one dipole is an H bonded to F, O, or N (atoms of high electronegativity) and the other end is F, O, or N ◼the strength of hydrogen bonding in water is approximately 21 kJ (5 kcal)/mol ◼hydrogen bonds are considerably weaker than covalent bonds ◼nonetheless, they can have a significant effect on physical properties R O H H O O R R R O H H O R R O H H O R